Stain and related composition



Patented May 7, 1935 UNITED STATES,

STAIN AND RELATED COIHPOSITION- Edward R. Bush, Lemont, 111., assignor to Chadeloid Chemical Company, New York, N. Y a corporation of West Virginia No Drawing. Application December 20, 19 32, Serial No. 648,137

25 Claim.

articles, such as wood articles, Stained with such compositions, various types of compositions including such stain bases, such as wood fillers,

lacquers, etc., articles carrying such composi-' tions, and methods of producing such stains and articles.

The present application is a continuation in part of application Serial No. 405,054, entitled Wood stains, filed November 5, 1929.

That prior specification is particularly directed to developments in the art producing new types of wood stains having properties of the greatest moment in the wood staining art. As there pointed out the wood stains of the prior art may be classified in three general classes, first, the water type, second the oil type', and third the spirit type. Each of these classes of prior art stains possess many undesirable features and attributes. The water stains which generally consist of aqueous solutions of water-soluble aniline dyes, applied to the desired surface in any de-' sired way as by brushing, due to the presence of the water-soluble aniline dyes were non-bleeding and non-fading, but such water stains very undesirably affected the grain of the wood by caus- I portant defect of such water stains was the fact that they have indifierent penetration, the dye remaining substantially on the top surface of the wood instead of impregnating the fibers. In spite of these defects and deficiencies of the prior art water stains, they probably constitute the bulk of stains used in that prior art, prior to the invention in applicants companion application identified above. This wide use of water stains was due to the fact that they were substantially non-bleeding and non-fading, attributes that were of prime importance in the wood staining art.

The oil stains while offering certain features of advantage as compared with water stains, displayed other disadvantageous characteristics. In general, they may be stated to consist of a hydrocarbon solution of an aniline dye base,-

treated, such as by maceration or other admixe ture with a fatty acid such as oleic or stearic acid to make the dye soluble in the stated hydrocarbon, such as benzol, toluol ora petroleum distillate. The oil stains have the desirable prop-- erty of penetrating into the wood surface, but 8 they are open to a number of very material objections. Owing to the preliminary treatment given the dyes torender them available in the oil stain compositions, the resulting product is not light fast, and is subject to the so-called 10 bleeding effect. Thus before a final topcoat of varnish or lacquer could be applied over the wood stained with the oil stains, an intermediate sealing coat of some kind, such as shellac; had to be applied. This was essential as otherwise the solvents of the varnish or lacquer will causethe bleeding effect referred to due to the stain penetrating into the varnish or lacquer composition. Further the presence of any excess of fatty acid in such oil stain compositions effects the practicability and the durability of the surface finish, producing such undesirable features as retarded drying and checking.

The spirit stains constituting the last of the prior art classes utilize aniline dye bases treated to be soluble in alcohol. They have not gone into very extensive use because they are subject to such undesirable qualities as lack of penetration into the wood surface, and lack of permanency of color due to fading qualities similar to those noted above in connection with the oil-type stains. Further the spirit stains are also subject to the bleeding defect, and in many instances also give rise to grain raising.

Accordingly it will be seen that each of the prior art types of stains are open to a number of objections, which have militated against their practicability and utilization in the prior art, and none of those prior art stain compositions is free from objectionable qualities for reasons pointed 40 out above.

In the prior application above identified, an entirely new type of stain has been produced possessing every desirable attribute for wood staining purposes, with freedom from the defects of the several classes of priorartwoodstains noted 1 above. These so-called permanent stains produced under the prior application possess the desirable attributes of penetration of the wood sur-' face to which they are applied without producing any substantial grain raising, and at the same time exhibiting non-fading and non-bleeding properties. The production of penetrating stains that are non-bleeding and non-grain raising, was effected for the first time in the art in connection with such compositions as those outlined in the prior application above identified.

The present invention also includes the produc-v tion of wood stains which have the property of penetrating the wood surface to which they are applied without any substantial grain raising, which possess substantial non-fading and nonbleeding properties, continuing such subject matter from that prior application, together with modifications of importance in the wood stain art.

Other objects and advantages include the production of combination stain and filler compositions, lacquer compositions, shading stains, etc., utilizing fundamental principles of this character.

Still further objects and advantages will appear from the more detailed description set forth below, it being understood, however, that this more detailed description is given by way of illustration only and not by way of limitation, since various changes may be made therein by those skilled in the art without departing from the scope and spirit of this invention.

In carrying out this invention we are more particularly concerned with the utilization of solutions of water-soluble aniline dyes. Water-soluble aniline dyes are preferably utilized because of their light stability and non-fading characteristics. While many of the solvent vehicles described below may be utilized desirably under special circumstances with oil and spirit soluble dyes earth colors, etc., more desirably the watersoluble aniline dyes are utilized because of their desirable properties, particularly for wood staining compositions. Further we may note that we are particularly concerned with solutions of such water-soluble aniline dyes. These various dyes may be employed under special circumstances in the form of dispersions, emulsions, pastes, etc. as indicated and exemplified below, but the wood stain composition per se is primarily made up of a solution of the water-soluble aniline dye.

As exemplary of water-soluble aniline dyes that may be employed in producing staining compositions under the present invention we may note the following: as blacks, Buffalo black NBR conc., No. 4523 Nigro black conc., acid black 10 BN conc., and nigrosine O, 3753; as reds, Azo Rubine EX conc., amacid brilliant croecine 3 BA conc., Azo Rubine X, croceine scarlet MOO conc.; as orange, orange A conc., and, orange Y; as yellow, fast wool yellow 3GL, and fast light yellow 2-G; as brown, Resorcine brown and Resorcine brown R0 2879; as green, alkali green 2 G0, and acid green 03442; and as grey, nigrosine 02 P powder. ,While this list of dyes referred to above is exemplary, the list actually given is comprehensive enough to permit the making of practically every common stain desired.

. As indicated, these dyes are most desirably employed in solution, and the nature of the solvents, diluents and vehicles employed materially influences the characteristics of the compositions, and the utilities to which they may be put.

As pointed out in the prior application, the most satisfactory class of solvents are those of the ether alcohol and specifically glycol ether type. As illustrative of the class of ether alcohols and particularly the glycol ethers, attention is particularly directed to such compounds as monobutyl ether of diethylene glycol, diethylene glycol monoethyl ether, and monoethyl ether of ethylene glycol. The solubility of aniline dyes in various solvents is not the same for all solvents, so that the solvent or solvent vehicle chosen must be determined in connection with the particular type of dye that is to be empolyed.

Diethylene glycol monoethyl ether is a particularly valuable solvent, since all of the desirable water-soluble aniline dyes used for wood stains appear to be soluble in this material. Monobutyl ether of diethylene glycol is also an excellent solvent for use in the present invention, but its solvent properties with respect to certain of the black aniline dyes, particularly of the nigrosine type, is less marked than that of diethylene glycol monoethyl ether itself. Monoethyl ether of ethylene glycol is also a desirable solvent, but like monobutyl ether of diethylene glycol does not have as great a solvent action on the aniline blacks as does diethylene glycol monoethyl ether. Diethylene glycol monoethyl ether is consequently looked upon as the best solvent for utilization in connection with the present invention, particularly in the production of wood stains.

While the ether alcohols, particularly the glycol ethers as represented 'by diethylene glycol monoethyl ether are particularly important solvents, as pointed out in the prior application, for utilization of these solutions of water-soluble aniline dyes, other solvent vehicles are also available particularly for use with particular water-soluble aniline dyes where the solubility is sufficient for the purposes in hand. Some of these additional substances, as specified below, have general solvent properties for the water-soluble aniline dyes, while others have restricted solvent action and may dissolve some of the water-soluble aniline dyes satisfactorily for utilization, without substantial solvent action or sufl'lcient solvent action on others of the water-soluble aniline dye class. Consequently, it is necessary where the chosen solvent has limited solubility for certain of these aniline dyes, to choose such solvents as are available for the particular dyes to be employed. Further as will be pointed out below in considering a number of these solvents, they frequently exhibit utilities for specialized purposes that have particular importance in special fields.

Triethanolamine may be particularly mentioned as a very desirable solvent for the water-soluble aniline dyes. In fact, its solvent properties toward the water-soluble aniline colors in general, may be compared with that of diethylene glycol monoethyl ether noted above. While the solvent effects of triethanolamine on the water-soluble aniline colors is comparable with diethylene glycol monoethyl ether as noted, it is not as desirable a material to employ in the production of wood stains for example, due to certain specific characteristics, such as its tendency to leave a greasy residue, and its extremely slow rate of evaporation. However, where triethanolamine is utilized inthe production of wood stains in accordance with the present invention, and in accordance with principles set forth below, the characteristics of the final composition may be compensated for by the addition of rapidly volatilizing ingredients that improve the properties of the composition. Triethanolamine may, therefore, be substituted for diethylene glycol monoethyl ether in some of the wood stain compositions specified below. In comparing such types of compositions, it may be noted that due to the faster rate of evaporation, with the diethylene-glycol mono-ethyl ether types of wood stains set forthbelow, one can safely recoat in as shorta time as one-half hour, whereas with the triethanolamine compositions a much longer time is required, and the greatest safety is obtained by not recoating until the next solvents may be employed. Among such there day after the application of the triethanolamine compositions.

Other types of solvents have more limited solvent effects on the water-soluble aniline dyes to the extent that they will dissolve some of these dyes but will not dissolve other members of the group, and this is particularly pronounced with may be noted glycerin, glycerol ethers, butyl lactate, triethylamine, the liquid chlorinated derivatives of diphenyl, ethylene glycol'and similar alkylene glycols, and sulphur treated oils and 'sulphonated oils, such as ichthyoL. As noted,

they maybe employed with those particular water-soluble aniline dyes which are soluble in the chosen solvent. Further such solutions may be modified by the addition of more rapidly volatilizing ingredients and other diluent components as explained below with other types of compositions inorder to secure more desirable properties for theparticul'ar purposes.

In the utilization .of the solvents referred to above, or other analogous and equivalent materials, they may of' course be utilized in various combinations. Thus mixtures of the glycol ethers may :be employed, particularly to fortify the solvent action of one upon the other. In

.-cases where monoethyl ether of ethylene glycol or monomethyl ether of ethylene glycol is employed having 'a more restricted solubility action on a particular dye, the action of such ether.

alcohol may be fortified by including diethylene glycol monoethyl ether ,in the composition. Similarly these ether alcohols may be employed in admixture with the other stated solvents of other types differing in character from the ether alcohols themselves. be employed for this purpose. The solvents other than the ether alcohols having restricted solubility action on various of the dyes may be used in admixture with the glycol ethers,.such as the diethylene glycol monoethyl ether. In this way it is possible to choose mixtures of these several solvents either to fortify the action of any particular solvent on a particular type of dye, or else to avoid extended use of more expensive solvents. Some of the solvents differ, of course, in cost from others, so that mixtures of solvents may be employed from this standpoint.

Compositions containing the dye and the high boiling point solvents referred to above, may of themselves be used without additional inclusions for various purposes. For example, the solution of the water-soluble dyes of desired concentration in any of the stated solvents, such as the glycol ethers including diethylene glycol monoethyl ether, or in any of the other solvents, such as triethanolamine, may be employed as a stain base composition. While the solution of the dyes in the high boiling point solvent are of themselves so slow evaporating as not to be particularly desirably used for wood stain purposes in general, these solutions may readily be converted into such wood stain compositions by the addition of volatilizing ingredients, water eliminants, etc. in accordance with the practice more fully set forth below in describing preferred types of wood stain compositions. The solution of the dye in the solvent, however, oiiers a commodity that may serve as an article of commerce, which may be shipped to wood stain users and converted by Any desired mixture may' the user himself into the final composition by the addition of added ingredients, such as for examplc the methanol and toluol ingredients referred to below, or other substituents of equivalent characteristics.

The concentration of the dye in the high boiling point solvent or other of the solvents set forth above, may be made as desired, so that a definite strength solution is produced to which the other ingredientsmay be added in controlled amounts to produce the final wood stain or other composition sought. q

Preferably, however, under these circumstances where .the compositions being manufactured and sold consist ofthe dye and high boiling point solvent, the concentration of the dye in the solvent is desirably increased materially beyond that required for a wood stain, so that upon dilution'with stated ingredients, the final wood stain composition is obtained.

In this way, dispersions,emulsions and pastes of the dye with other components may be produced, whether the additional components be the high boiling point solvents, low boiling point ingredients such as rapidly volatilizing ingredients and water eliminants, or other solvents, diluents and vehicles, so long as the quantitiesof such liquids present, are not suflicient to convert the dye into a true solution. In this way, the concentration of the dye in the vehicle may be made as desired, and a very concentrated composition produced either in the form of a dispersion, emulsion or paste, which may bediluted with other ingredients to be utilized for wood stain or other purposes as set forth below. Thus any of the stated dyes set forth above may be utilized with diethylene glycol monoethyl ether, for example, the proportions of ingredients being such that there is insuflicient diethylene glycol monoethyl ether present to dissolve all of the dye, and the amount of dye present being sufficient to yield a. paste upon intimate incorporation of the ingredients. This material makes a paste which upon dilution with other ingredients may be con verted directly into a wood stain for example. As a matterof fact, the treatment of the dye with the diethylene glycol monoethyl ether alone for the production of such types of materials is desirable because it has been found that some of the more diflicultly soluble dyes upon standing in contact with such high boiling solvents as diethylene glycol monoethyl ether and other of the ingredients set forth above, are more readily converted into soluble form and are more readily converted into the final solution upon addition of the more volatile ingredients, etc. As exemplary of proportions to be utilized in produring such pastes, dispersions and emulsions in which the dye is not completely in solution in the vehicle present, there may be used amounts in excess of those set forth below in connection with may be employed, in solution in highly volatile ingredients for the purpose of producing compositions having particular utilities under limited circumstances. Within this classof compositions we may mention the so-called shading stains. Shading stains are employed for application to a particular spot where a deficiency of color ex- ,and lacquer coats, or between the sealer and lacquer coats. Thus when a first coat of lacquer has been applied, the gloss of this coat naturally reveals any slight imperfections in color which may have been missed in the staining and filling operations. The use of a shading stain may be employed therefore to correct such slight imperfections by spot spraying as referred to above. For such shading stains any of the water-soluble dyes referred to above may be utilized in highly volatile components many of which are set forth below in connection with other compositions. The alcohol type of solvents may desirably be employed, and among these synthetic methanol is particularly satisfactory in making up a shading stain. Synthetic methanol has been found to have highly satisfactory solubility for some of the water-soluble anilines, for resorcine brown and some of the greys. Its solubility on some of the reds is slight, and it exhibits practically no solubility on the other water-soluble anilines than those discussed above. However, the solubility of the synthetic methanol for the greys and browns and for a trace of red when required. gives a range satisfactory to fill the necessities for the ordinary purposes for which shading stains are employed. While the synthetic methanol solution of the stated water-soluble aniline dyes as given above, is particularly emphasized for use as a shading stain, it is possible also to utilize solutions of these dyes in other of the more volatile solvents set forth below for analogous purposes.

These shading stains which may also be employed as blending stains, are particularly effective for the purposes stated because of their rapid drying, and their ready application and use over filler, sealer and lacquer coats.

While various types of special solutions, emulsions, dispersions and pastes as describedabove, may be employed for particular purposes, by far the most important utility of these compositions is in the production of wood stains that are light fast and penetrating, and which. .are'non-fading, non-bleeding and non-grain raising. In the production of such stains, composite solvent vehicles are employed, which include not alone the high boiling point solvents set forth above, particularly solvents of the character of the glycol ethers, such as diethylene glycol monoethyl ether, and also such components as triethanolamine in view of the solubility of a wide range of such watersoluble anilne dyes in such stated solvents, but also including rapidly volatilizing ingredients. The vehicle employed should be a penetrating vehicle and the term penetrant vehicle is used herein to cover that characteristic of these wood stain compositions containing water-soluble aniline dyes in solution in composite solvent vehicles that penetrate and carry the dyes substantially into the wood, instead of merely to deposit it upon the surface of the wood only as in the case of water stains. The vehicle in carrying the stain or dye into the wood and below the mere surface portion thereof should subsequently evaporate rather rapidly leaving the pores of the wood impregnated with the stain. Furthermore, the penetrant vehicles should exhibit a proper evaporation curve to dispel all of the components including the high boiling components such as diethylene glycol monoethyl ether and other ingredients, and any moisture present. Compositions exhibiting such smooth evaporation curves are particularly desirable in this connection and are well illustrated by some of the preferred composite vehicles set forth below.

The compositions should not exhibit any undesirable hygroscopic effect, and the action of the solvent vehicle should be such as to distribute the stain desirably over the top layer of the wood and through the under fiber in order to secure uniformity of color, but penetration should not be so great as to result in substantial waste of dye or uneven deposit of color on the surface.

As noted above, one of the mostimportant components of such solvent vehicles for the production of wood stains are the high boiling liquids of the ether alcohol group, particularly the glycol ethers as represented by diethylene glycol monoethyl ether, monobutyl ether of diethylene glycol, monoethyl ether of ethylene glycol, and monomethyl ether of ethylene glycol referred to above, the diethylene-glycol mono-ethyl ether being preferred in this group because of its solvent action on practically the entire range of water-soluble aniline dyes. The production of wood stains of penetrating light-fast characteristics, that are substantially non-fading, non-bleeding and nongrain raising, may, therefore, be exemplified by the glycol ether solutions of the water-soluble aniline dyes. These compositions as noted above produce an excellent stain base, but for use for wood stains are preferably utilized with addi-' tional solvent and vehicle ingredients particularly to overcome slow drying and hygroscopic properties of such high boiling materials as diethyleneglycol mono-ethyl ether and other of the solvents referred to. The choice of such additional solvents, diluents and vehicles involves a consideration of the factors referred to above, including the production of smooth evaporation curves, securing penetration of the dye to the desired extent, uniform dying over the surface of the wood article treated, and light fast, non-fading, nonbleeding properties, and particularly the absence of grain raising characteristics. solvents, diluents and vehicles utilized should preferably be relatively inexpensive so that the products may be commercially practicable for wide use. Desirably the solvents, vehicles or diluents should be miscible with the dye solutions to a yield homogeneous compositions. The presence of water eliminant properties in the composition is particularly desirable in order to give resistance to moisture retention.

The production of woodstains will be particu- Further larly emphasized by three component vehicles acting as a solvent. vehicle for the water-soluble aniline dyes referred to above. The high boiling solvents will be exemplified in the use of diethylene glycol monoethyl ether, which is considered by far the best of the high boiling solvents for use in the production of wood stains. The class generally of glycol ethers is preferred in this connection, but the trialkylol amines, such as triethanolamine, may also be specifically referred to, triethanolamine probably being the widest range solvent for the class of water-soluble aniline dyes referred to other than the glycol ethers, particularly such as diethylene glycol monoethyl ether.

Of the other components desirably utilized, components are chosen which increase the rapidity of drying and setting of the composition. Among these then may be mentioned the aliphatic alcohols such as methyl and ethyl alcohols,

32,000,120 ketones such as acetone, and the esters of the aliphatic alcohols, particularly the fatty acid esters such as ethyl acetate, etc. Methyl alcohol or synthetic methanol is a particularly valuable ingredient for use in this connection.

An additional ingredient is desirably employed in the composition selected from the group including hydrocarbon distillates, particularly the coal tar distillates, petroleum distillates, benzol, toluol, solvent naphtha, the xylols, ethyl benzene, etc. Toluol is particularly useful in this connection. Many of the esters referred to in the group of components above, including such esters as I butyl propionate and butyl acetate are exemplary of materials also having water eliminant properties, but such materials,as these esters being slower drying and more expensive, are more desirably substituted by such components as hydrocarbons, particularly toluol. Petroleum distillates available on the market within limited ranges of boiling points suggested as substitutes for toluol may be employed, but toluol has been found to be a particularly desirable ingredient in these compositions.

Both of these groups of materials, particularly the aliphatic alcohols and the hydrocarbon distillates and their equivalents aid in the penetration and evaporation and other desirable effects sought in these wood stain compositions.

One of the most desirable composite solvents for use in the production of these wood stains includes the following, the parts being by volume:

1 part diethylene glycol monoethyl ether 9 parts methyl alcohol 6 parts toluol Such composite solvent vehicles are utilized for solution of the particular dye desired. These I composite solvent vehicles themselves are, of

course, utilizable as articles of commerce, and may be sold for use to dye manufacturers or to wood stain users.

A solvent vehicle of the character set forth above may for example be used to dissolve from 1 ounce of dye per gallon of vehicle to higher amounts; depending on the solubility of the dye and other factors. The amount of dye utilized depends on the particular dye itself, and its degree of concentration, and of course the depth of color required in the particular stain. Further the strength of the dye stain may be varied, for example, by the amount of diethylene glycol monoethyl ether utilized.

In making up compositions utilizing such composite vehicles, it has been found preferable to allow the aniline dye, particularly when of the less soluble characters, such as the nigrosines, to stand with the diethylene glycol monoethyl ether until solution is obtained, after which the other ingredients may be added. And preferably also it has been found desirable after solution has been obtained in the diethylene glycol monoethyl ether to add the alcoholic ingredients, such as the methyl alcohol before the addition of the toluol since the diethylene glycol monoethyl ether with the methanol appears to' exert a very desirable solvent action on the dye.

The solution of the chosen dye in the vehicle set forth above gives an excellent wood stain having desirable drying properties and rapidity of setting, a proper evaporation curve, etc. The proportions of solvents and ingredients in this composite solvent may, of course, be varied within substantial limits, and of course various combinations of stated ingredients may be utilized,

and equivalents employed for the materials set forth in this particular composition.

To increase the dye strength of the stain composition when desired, there may be employed:

3 parts diethylene glycol monoethyl ether '9 parts methanol 4 parts toluol This composite solvent mixture may be used in connection with 3, and in some cases 4, ouncesof the aniline dye per gallon of the composite solvent. Other mixtures include 1 or 2 parts by volume of diethylene glycol monoethyl ether to 9 parts of methanol and 5 parts toluol. But it should again be noted that these compositions are given merely by way of illustration to exemplify very desirable types of stain compositions that may be utilized for that purpose; and as noted above, these additional solvents and the rapidly drying ingredients, such as methanol, water eliminants, etc. may be substituted by other ingredients or combinations of stained ingredients may be employed.

The following will illustrate the application of such stain compositions to wood, particularly to emphasize the simplified methods which result from the utilization of the present compositions. In treating an open grain wood, for example, such as oak, the wood may be stained and then the stain allowed to dry. Following this a filler, such as a silex filler may be rubbed in, and following the filling treatment a lacquer or varnish may be applied. In treating a close grain wood, such as birch for example, the stain may be applied to the wood article and then allowed to dry, followingwhich the lacquer or varnish or other finishing coating composition may be applied. Thus it is seen that not only are the staining methods considerably simplified and made more economical by the use of the stain compositions of the present invention, but stains are obtained which are substantially light fast and consequently do not fade, which stains are further non-bleeding, which stains further penetrate into the wood and give uniform staining operation, and which furthermore do not raise the grain of the wood. Stains possessing all of these characteristics it is believed'have been produced for the first time in the art by the use of such com positions as those set forth herein.

It may be well to consider some of the functions which these ingredients exhibit in these wood stain compositions that enable the new results to be obtained. But in giving such explanations as those set forth immediately below, it should be understood that these-considerations are not intended to be limiting, because the results obtained by the utilization of the compositions set forth herein have been demonstrated in practice, and it is immaterial whether the explanations given below are accepted. The diethylene glycol monoethyl ether solution of the dye, of itself, is rather slow drying and hygroscopic, so that it does not offer the best type of material for direct use as a wood stain.- Consequently although-the diethylene-glycol mono-ethyl ether is primarily the color carrier and exhibits a certain degree of penetration, of' itself, it does not give the preferred wood stain compositions. Even with the inclusion of toluol in the diethylene glycol monoethyl ether solution of the dye, there is a tendency to gather moisture, and the composition is still rather slow drying, and there may be some tendency, in come cases to raising the grain of the wood. The'inclusion, therefore, of the aliphatic alcohol, particularly the methanol gives the most desirable result. The action appears to take surface of the wood: the alcohol passes off into the air; the toluol remains as a bailie plate to moisture and evaporates next; and the final action of the diethylene glycol monoethyl ether is soaking up by absorption into the fibers of the wood. At the start of this absorption action, the color is still held in solution by the remaining diethylene glycol monoethyl ether, and when this latter evaporates finally, the color. has been deposited into the wood as a dye, without any residue of coloring matter, as would be the case with water stain. Thus there is a, very even distribution of the color, both through the under fiber and on the top layer of the wood. This leads to the uniformity of color effect which is obtained by these stain compositions, and also marks substantial economy in the use of the color. Further it apears that the effectiveness of the color action in the diethylene glycol monoethyl ether.

penetrating wood stain is very much greater than in any of the other stains of the prior art where much of the stain is wasted, either by too deep penetration, or more particularly by uneven deposit of color on the surface where it is too thickly deposited at some point. Furthermore, it should be noted that mere deposit on the surface as was obtained with many of the prior art stains does not give the brilliancy or lustrous effect, or bring out the grain of the wood which is desired in high grade wood staining, and which issecured by the present stains. These stains it should be noted produced under the present invention stain both by adsorption andabsorption, so that uniformefiects are obtained with woods that may vary considerably in their very nature.

The specific example set forth above utilizing methanol, toluol and diethylene glycol monoethyl ether in the proportions of 9:6:1 parts by volume for solution of 1 ounce, for example, of aniline dye may be referred to as a typical formula for what may be denominated a single strength solution; More concentrated solutions may desirably be manufactured as stock solutions to be kept on hand for dilution to the final desired strength. Thus a triple strength solu tion may be made up from the following formula:

72 ounces methanol 32 ounces toluol 24 ounces diethylene glycol monoethyl ether 3 ounces aniline dye to 1 gallon of above mixture Or weaker solutions may be made if desired, and a typical formula for a double strength solution would be:

2 ounces of aniline in a gallon of 9 parts methanol 5 parts toluol 2 parts diethylene glycol monoethyl ether The single strength solvent mixture given a ratio of 2 parts methanol to 1 part diethylene glycol monoethyl ether utilized for dilution.

When triple strength solutions of the basic colors are utilized for stock, such mixtures are usually too strong for ordinary use, and they may be reduced todesired strength by dilution with a thinner, which may consist for example of 2 parts methanol 1 part toluol This practice enables the stocking of triple strength solutions for example and subsequent dilution, so that the minimum amount of stock may be kept on hand. Or of course, the triple strength solutions may be utilized as articles of commerce and sold to the same users for dilution and reduction by the user. The maintenance of triple strength stock solutions in basic colors enables these to be mixed as desired to produce particular shades, and this of course applies also to single and double strength solutions.

In the use of these stains, high lighting operations may be performed immediately after the initial staining of the wood, either by the heavier application of the stain in use, or by the use of another gun in the same spray booth connected to a permanent penetrating stain of the desired color or intensity.

-As pointed out above, wood stain compositions produced under this invention exhibit no substantial grain raising properties. While some of the lower aliphatic alcohols such as methyl and ethyl alcohols by themselves it directly applied to wood produce grain raising in the same way that water does, the presence of other components avoids any grain raising effects in the compositions set forth herein. Similarly grain raising effects due to the presence of such components as diethylene glycol may be avoided in the same way by the presence of other components -in the solvent vehicle.

Instead of using one of the solvents such as diethylene glycol monoethyl ether or triethanolamine, which is a complete solvent for the dyes referred to, a composition may be utilized employing some of the other solvents such as monoethyl ether of ethylene glycol or monomethyl ether of ethylene glycol, and these may be employed with some of the dyes which are not completely soluble therein, by the utilization of a small amount of water to obtain complete solution of the dye. While such water-containing compositions are not preferred, they may be utilized as set forth, and the choice of water eliminants and other volatile ingredients may be made in accordance with the disclosure set forth above, to secure an evaporation curve of desirable characteristics, which will also remove the water present in the compositions without grain raising effects.

Further it should be noted that while three component solvent vehicles are particularly emphasized above for the production of the most desirable types of permanent stains, two component vehicles may be employed, such as for example diethylene glycol monoethyl ether and methanol. Thus a stain of. one of the dyes in solution in diethylene glycol monoethyl ether and methanol may be desirably employed as a practical stain under limited conditions, the main difficulty being that in humid weather there is considerable sensitiveness to grain raising. The inclusion of toluol in the composition in accordance with the formulas given above, produces a product that can be utilized day in and day out under all ordinary conditions.

For some particular purposes, in the utilization of wood stains, it may be desirable to check thepenetration of the stain into the wood. .The degree of penetration secured with these wood stains can be readily controlled by the incorporation of film-forming components, such as resins, either natural or synthetic, but preferably the latter, nitrocellulose, etc. Nitrocellulose lacquer compositions are particularly desirable in this connection. Thus when it is desired to check the penetration on end wood and carved wood sections, a lacquer may be added to the wood stain composition utilizing, for example 20% of lacquer. Or nitrocellulose may be dissolved up directly in the wood stain composition to the desired extent and for the same purpose either with or withoutadditional solvents, diluents and vehicles. The degree'of penetration secured under such circumstances may be readily controlled by the proportion of film-forming component, such as nitrocellulose that is included in the composition.

0n the other hand the water-soluble aniline dyes either of themselves or in the wood stain bases or wood stain compositions set forth above may be added to or incorporated with cellulose ester or ether solutions and lacquers, as well as other types of lacquers particularly those containing solvents of the nature of alcohols and hydrocarbons, in order to produce lacquers having light fast colors. Color, dipping lacquers may be produced in this way. The nitrocellulose or other cellulose ester or ether solution may be combined with the wood stain composition as set forth above, or the cellulose derivative may be dissolved in the wood stain composition. As noted above, sufficient nitrocellulose or other cellulose derivative may be incorporated in the composition to prevent any penetration of the dye into the Wood surface where these compositions are applied directly to the wood surface, or the amount of nitrocellulose may be limited to secure penetration to a limited extent in the under wood surface. Of course, such lacquers may be applied directly to the wood surfaces, or more desirably as in usual practice, the lacquers may be applied over other base coatings, such as sealers, etc. Particularly it should be noted that the lacquer compositions including the water soluble aniline dyes may desirably be employed as top coats over wood stained With the present stains, or after the application of combination stain and filler compositions as set forth below. Where complementary dyes are employed in the lacquer solution to those employed in the initial wood stain or stain and filler combination, -or where the dyes are the same, a materially heightened effect of depth is secured in this way.

Most important eifects are secured by the utilization of lacquer coatings over the wood stain compositions of the present invention as compared with prior art practice. In view of the properties of these wood stain. compositions as set forth above, the lacquers may be applied directly over such wood stain compositions Without securing bleeding, and further the lacquering operation may be carried out in a relatively short time after the application of the initial wood stain composition-a result which cannot be obtained in the prior art where very substantial periods of time must elapse before the application of lacquer coatings, and where also sealing coats are required as set forth above in order to avoid bleeding.

' One particular utilization of nitrocellulose type compositions containing these water-soluble aniline dyes may be mentioned, and this is the finger nail enamel field. While in this connection, nitrocellulose compositions are being employed, the art is essentially distinct from the ordinary nitrocellulose lacquer art, because when coating compositions of the nitrocellulose type are ordinarily employed for coating articles of manufacture, they must possess certain properties yielding non-blushed smooth coatings, which considerations are of secondary character in finger nail enamels. Consequently, it is possible to produce finger nail enamels under the present disclosure using cellulose derivatives, such as nitrocellulose, with water-soluble aniline dyes, all in solution in a solvent vehicle, which of itself would not be satisfactory for ordinary nitrocellulose lacquer type coatings, but which is eminently suited for finger nail enamel use. Thus the synthetic methanol solution of the water-soluble aniline dyes set forth above for use as a shading stain, may be converted into a finger nail enamel by the inclusion of nitrocellulose. Such a composition is very rapid drying and gives a satisfactory finger nail enamel. Of course, the compositions may be more complex and may include the glycol ethers as set forth above, particularly utilizing the latter as color carrying agents for the watersoluble aniline, the glycol ethers of course also being very desirable solvents for the cellulose derivatives, particularly. nitrocellulose. Thus a composition containing diethylene glycol monoethyl ether or other glycol ether with methanol, nitrocellulose and a water-soluble aniline dye may very desirably be used as a finger nail enamel. particularly desirable because they do not change in color and do not turn brown a very undesirable characteristic of prior art finger nail enamels); they do not fade badly or quickly or completely lose their color, and they yield a very satisfactory coating of intense color when this is desired.

Another field of development possible under the present invention is in the use of combination stains and fillers for the treatment of wood surfaces. Thus light fast combination stain and fillers free from the defects of prior art compositions enabling staining and filling to be accomplished in a single operation is possible under the present invention.

Any of the ordinary wood filler materials, such as silex, corn flour or corn starch, wood flour, etc. may be incorporated in such combination stains and fillers, the incorporation being made with a permanent stain composition in accordance with the examples given above. It is possible in producing combination stain and fillers Any of these finger nail enamels are 5 in accordance with the present invention to eliminate the presence of oxidizable oils, such as the drying oils from such compositions, and to duces other difliculties such as graying of pores,

blistering, etc. The wiping off times with these combination stains and fillers are also within the period necessary for commercial "operation. While, therefore, under the present invention, combination stains and fillers eliminating the use of any drying oil is obtainable, thecombination stains and fillers produced by the use of drying oils are also included, and an example thereof is given below. In'the combination stain and fillers omitting drying oils, the initial filler pastes which are included with the stain compositions in the development of the final products are desirably made up using resins, either natural or synthetic, such as dammar, rosin, ester gum, phthalic-glyceride resins, particularly the phthalic-glyceride resins which include in their constitution glyceride oils, or the fatty acids derived from such glyceride oils. The following example illustrates the production of an excellent combination stain and filler, with no drying oil utilized in the composition.-

A filler paste is firstprepared as follows: 13 ounces (weight) fine silica l 3 ounces (weight) corn starch ounce (weight) wood fiour I 9 ounces (liquid) dewaxed dammar solution 1 ounce (liquid) diethylene glycol monoethy ether 1 ounce (liquid) butyl lactate The dewaxed dammar solutionmay be made by dissolving natural dammar resin in a mixture of ethyl acetate, ethyl alcohol, methyl alcohol and toluol', and the composition then allowed to stand and settle, the wax naturally present in the dammar being completely precipitated and the clear dammar solution secured by decanting or equivalent process. This is merely exemplary of the production of a dewaxed dammar for use in this connection:

The combination of fine silica, corn starch and wood fiour is particularly effective in these wood fillers.

The permanent combination stain and filler, which also exhibits scaling properties, is then made as follows:

. %th ounce (weight) orange water-soluble aniline dye %ths ounce (weight) black nigrosine soluble aniline dye 2 ounces (liquid) diethylene glycol monoethyl ether 14 ounces (weight) filler paste 4 th ounce (weight) Van Dyke brown A ounce (liquid) butyl acetate 2 ounces (liquid) methanol 1 ounce (liquid) toluol These ingredients may be combined in any desirable way, one such method including the solution of the dyes in the carbitol, the incorporation of the filler paste and pigment with the butyl lactate, followed by incorporation of the methanol and toluol, and the final addition of the diethylene glycol monoethyl ether solution of the dyes.

This composition utilizing dewaxed dammar solution is particularly useful as it exhibits except'ional sealing properties to subsequent excoats of lacquer or other finishing coatings. That is, where ordinary filler exerts a great deal ,of suction on finishing coats or material, which is its nature.

resins in combination with polymerized China wood oil by the cooking process, may be employed. In lieu of butyl lactate, other components may be used, and particularly reference may be made to the use of creosote oil in lieu of the butyl lactate. The use of such components as creosote oil and butyl lactate in these formulations exhibit a very novel and desirable efiect. When a creosote oil containing composition filler is applied to wood by either brush or spray, the physical performance appears to be something of the following: first there seems to be a separation of the solvent, then evaporation starts. A portion of it penetrates in combination with other solvents, and yet another portion seems to cling on the top of the filler which is drying. This top surface portion is best described as greasy-like in It holds the filler "open by retarding its natural tendency to dry fast and to cake into a hard mass. When the wiping ofi operation of the excess filler occurs, this fact is important because it makes the filler slide, as though the pigments were lubricated, and thus permits eflicient cleaning up which is of vital practical importance. Such desirable qualities are imparted to the filler by these materials, such as creosote oil of relatively very low cost. And the lubricity functionthus secured while somewhat impairing ideal filling, gives a very satisfactory practical filling .job. for; ordinary purposes. Similarly in connection with "butyl lactate, this has an excellent activity in these compositions, although it is somewhat higher in point of cost. 'Butyl lactate holds thefiller open ina practical and desirable manner, permits of wiping off with ideal packing of the pigment in the pores of the wood,

andfblends in nicely over coats of lacquer or butyl lactate appears to assist to some extent by partially dissolving and holding in better solution certain of the typical water-soluble aniline colors that go to make up the coloring matter of the combination stain and filler. It has rather fair solubility for brown and yellow, light red is partially soluble, black slightly soluble, and other colors, suc as dark red and orange, of poor solubility, although it does exert some action on them. Due, therefore, to the solubility action of the butyl lactate, it is possible to reduce the normal amount of diethylene glycol monoethyl ether by the assistance rendered through the partial solvent action of the butyl lactate.

In lieu of the creosote oil referred to above, other liquids of similar character, such as rosin oil, maybe utilized, but their action is-not so desirable because they have a tendency to interfere with good adhesion of subsequently applied lacquer or varnish coats.

As exemplary of a combination stain and filler produced utilizing a drying oil, there may be mentioned the production of a paste by the use of polymerized China wood oil, either with or without combination with resins, the paste being made up from such material together with silex, and desirably also corn starch employing inert pigments, typical of which there may be mentioned Van Dyke brown, ferrite yellow, the umbers, and the siennas, together with wood flour as a fourth ingredient of this combination. Of this combination of materials, the corn starch may constitute 10% of the entire pigment combination, and the inert pigments from 10 to 25% thereof. Slate with a stain reducer, such as 2 parts methanol to 1 part toluol. Finally the color carrier, diethylene glycol monoethyl ether, is incorporated carrying the desired aniline colors in the proportion of 4 to 6 ounces of aniline color to a quart of diethylene glycol monoethyl ether. The admixture of these ingredients, preferably in the order specified, gives the finished product.

Certain considerations of a general character may be noted in this connection. The earth pigments are desirably employed to reduce the cost, to give added color, and most important to prevent any graying out in the pores caused by the action of the lacquer on the silex, which is naturally gray white in color. The cornstarch may desirably be employed, because it helps to bind the earth colors to the silex. An explanation of this may be offered along the following lines. .In contact with the diethylene-glycol mono-ethyl ether, some action appears to take place between the corn starch and the diethylene-glycol' monoethyl ether, which upon evaporation produces a cement-like action, which causes earth colors such as Van Dyke brown, umber, sienna, etc. to be literally glued to the silica and thus to prevent graying of the latter that usually occurs when lacquer is applied over a silica paste filler.

The wood flour is desirably employed as a component of these fillers to retard drying and to keep the surface moist for a longer wipe-ofl.

Plasticizers like the tricresyl phosphate mentioned above are desirably included in the composition in order to improve the elasticity thereof, and also because here too this ingredient extends the drying time for wiping off.

As pointed out above, butyl lactate and creosote oil are also desirable ingredients employed as set forth above, because they too tend to keep the film open during the drying operation.

Several of these features are particularly important in connection with combination stain and fillers, or other types of fillers that do not contain adryingoil. Thedryingoiltypesoffillers have longer drying periods, whereas the types of fillers set forth above omitting any drying oil, are much more rapidly drying. With these non-drying oil containing fillers, it is necessary to secure a sumciently long drying period to enable the wiping off to be satisfactorily carried out. This has been eminently accomplished in connection with the fillers described above, and the particular components that may be desirably utilized in this connection, although it should be noted that they are exemplary and are not intended to be limiting.

Another important feature is the fact that the fillers of the character set forth above, particularly those carrying the gum type solutions, if such gum solutions are replaced by solutions of dewaxed shellac, for example, fillers are obtained having excellent sealing properties, which is particularly desirable in holding subsequent coats of lacquer as topcoats and other similar types of finishes. Such stain filler sealer combinations are wellexemplified by the combination stain and filler given above using the dewaxed dammar solution, and other gum and lacquer type preparations free from drying oils may also be utilized as exhibiting satisfactory sealing properties, and may therefore be used as sealer coats.

Some of the important features that may be emphasized in connection with these combination stain and fillers, and also combination stain and fillers which may also be used as sealers, are the following: the staining, filling and sealing operations may thus be carried out in a single step, leaving the surface directly ready for the building coat. These compositions are, of course,

light fast, and do not raise the grain of the wood.

They may be brushed, sprayed or applied by dipping. Applied like ordinary oil type fillers, they may be wiped in a very short period. They may be coated with shellac, lacquer sealers, or body lacquers the same day, orovemight, al': though in emergencies such overcoats may be applied in a relatively few minutes. They insure proper adhesion of lacquer which is impossible with oil filler, certainly on a commercial scale.

Much more uniform effects are obtained than with water stains, followed by oil filler, in accordance with preferred practice of the prior art,

and for the most part no toning is required,'but this if decided upon may be accomplished by toning immediately with the permanent stains set forth above. These combination stains and fillers will cover a great deal more surface than the ordinary oil filler. The components remain in suspension, requiring little stirring. Far better impregnation of the wood is obtained than with the prior art types of oil fillers, due primarily-to penetration. They hold out overcoats much better than does the prior art type of oil filler, this being the sealing feature particularly referred to above. They do not bleed into lacquer or varnish.

It is pointed out above that a particularly valuable feature of the wood stains and combination wood stains and fillers produced in accordance with the present invention lies in the fact that they may be utilized, and topcoats of lacquer and varnish and of other types may be directly applied without bleeding and other undesirable properties, and without requiring the use of intermediate sealing coats. Of course, if desired inter- .mediate sealing'coats of one type and another by weight of a stated water-soluble dye.

The following illustrates a wood stain utilizing a small amount of water in the composition, the water content being insufiieient to cause substantial grain raising in view of the other components of the mixture.

36 ounces methanol 16 ounces toluol 11 ounces diethylene glycol monoethyl ether 1 ounce water The proportions stated above are by volume, and are utilized with 1% ounces by weight of the desired water-soluble dye. In compounding the mixture as stated above, the dye may be cut in the water, the diethvlene glycol monoethyl ether 1 0 then added, followed by additions of the methanol and toluol.

In exemplifying the use of these dyesolutions with lacquers to produce colored lacquers, it has been pointed out that the amount of film-forming ingredient, whether it be a synthetic resin or a cellulose derivative, may be utilized to determine the extent of penetration of the dye into a wood surface ,when used thereon. Of course, in the usual case where a coating composition is desired, substantial penetration of the dye is not sought, and the discussion above enables the production of lacquers of various types as coating compositions. In such nitrocellulose lacquers-for example, any of the ingredients ordinarily employed as solvent vehicles or diluents may be utilized, provided that they are compatible with the dyes employed in the solutions. As illustrative of such ingredients, there may be utilized the aliphatic alcohols, such as methyl, ethyl, propyl butyl, isobutyl, andamyl, ketones, such as acetone, the esters of the aliphatic alcohols, and particularly the fatty acid esters of such materials, such as ethyl acetate,butyl acetate, amyl acetate, etc., plasticizers and softeners, such as ethyl phthalate, butyl phthalate, dibutyl phthalate, triphenyl phosphate, tricresyl phosphate, etc. In such nitrocellulose lacquers and other types of compositions for coating purposes, there may also be included resinous ingredients, including the various resins both natural and synthetic, such as the natural resins, rosin, dammar, congo, and the chemically modified natural resins, including rosin ester, acetylated congo, etc. The synthetic resins include the phenol-formaldehyde types of resins, oumarone resins, vinyl resins. phthalic-glyceride types of resins, etc. In such cases, the resins chosen should be compatible with the cellulose ester of the composition, and of course should not precipitate out the dye components to any substantial extent in the particular formulas employed. The phthalic-glyceride resins are exemplary of synthetic resins that are compatible with the nitrocellulose and the other elements of the composition. Among the phthalic-glyceride typesof resins there may be specifically mentioned the phthalic-giyceride resins produced with a fatty oil component, either the oil itself, or fatty acids derived from the oils, such fatty oil component being tied up in the resin molecule. Fatty acids of the drying oils are particularly desirable as combined elements in such phthalicglyceride resins.

D'yed lacquers produced in accordance with the present invention may desirably be used for coating various articles of manufacture whether such articles are made of wood, metal, glass,

paper, fabric, leather, etc., and the dyed lacquers of the present invention may represent one of sevand coats applied to such articles, the dyed lac- .quer being a topcoat applied over other initial coats, or the dyed lacquers of the present invention may be intermediate coats with other coats applied above them.

The following will exemplify a dipping lacquer produced in accordance with the present invention:

12 ounces methanol 10 ounces toluol 9 ounces xylol 8 ounces amyl acetate 8 ounces butyl alcohol 1 ounce castor oil 16 ounces gum solution The above components are given in parts by volume. The gum solution is a solution of a glycerin-phthalate resin in coal tar solvents. with such vehicle, there may be employed 8 ounces by weight of nitrated cotton, such forexample as the alcohol-soluble variety, and for the dye component there may be used 2 ounces by volume of a permanent strain composition produced as set forth above.

These components are incorporated together to produce a dippin lacquer.

While lacquers in the nature of coating compositions may thus be desirably produced as explained above, a particular feature of the present invention lies in the inclusion of a limited amount of lacquer or other film-forming ingredient to check partial penetration of the stain. As exemplary of a particular composition to be employed in this connection, we may utilize the following:

27 ounces methanol 12 ounces toluol 9 ounces diethylene glycol monoethyl ether This vehicle may be employed in the parts given by volume with Hths ounces by weight of watersoluble dye and 16 ounces by volume of nitrocellulose lacquer. The nitrocellulose lacquer may consist of 10 ounces of nitrated cotton to 1 gallon of lacquer solvents and diluents, no resin or plastioizer being present in the composition.

As exemplary of other types of compositions that may be employed as set forth hereinabove for use as finger nail enamel compositions, there may be noted specifically the use of 12 ounces of a clear lacquer, such as is standard for finger nail clear lacquer, with this ounces of water-soluble dye, dissolved in 6 ounces of monomethyl ether of ethylene glycol.

Or another type of finger nail enamel composition might be made from 7 parts of a standard nnger nail lacquer, with 1 part of permanent As further exemplary of a combination stain and filler. the following composition may be employed:

By weight 8 ounces fine silex 12ounces medium silex 3 ounces corn starch 2 ounces dry color 14% ounces gum solution 12 ounces methanol 5 ounces butyl lacetate 10 ounces refined coal tar naphtha 3 ounces rape seed oil By weight 1 ounce water-soluble dye By measure 10 ounces diethylene glycol monoethyl ether This combination of ingredients incorporated together as explained above in the production of combination stain and fillers gives an excellent combination stain and filler.

Having thus set forth my invention, I claim:

1. A wood stain containing a water-soluble aniline dye in solution in a penetrant composite vehicle containing a high boiling organic solvent for the dye and a compatible low boiling organic component, the ingredients being present in proportions to yield a wood stain of light fast, nonfading non-grain raising properties and not bleeding into lacquer and varnish topcoats.

2. A wood stain as set forth in claim 1 containing triethanolamine as the dye solvent.

3. A wood stain as set forth in claim 1 containing mono-ethyl ether of ethylene glycol as the dye solvent Bymeasure claim 10, in which the dispersion medium is a 4. A stain base composition capable upon dilution of yielding a wood stain, said base containing a water-soluble aniline dye and a high boiling organic solvent therefor, said composition being adapted upon dilution with methanol and toluol to yield a penetrating wood stain of light Iast, non-fading non-grain raising properties and not bleeding into lacquer and varnish topcoats.

5. A stain base composition capable upon dilution yielding a wood stain, said base containing a water-soluble aniline dye and a triethanol amine solvent therefor, adapted upon dilution with methanol and toluol oi yielding a wood stain that is substantially light fast, non-fading, nongrain raising, and not bleeding into lacquer and present in proportions to yield a substantially light Iast, penetrating, non-bleeding, non-grain raising stain.

7. A shading stain consisting of a watersoluble acid aniline dye in solution in a rapidly volatilizing organic solvent. I

8. A wood stain base containing a light-fast aniline dye in solution in a vehicle containing a component selected from the group containing glycol ethers and triethanolamine.

9. As a wood stain: a water soluble acid dye in solution in a volatile penetrating organic vehicle.

10. A dye in organic dispersion comprising a dye material normally insoluble in the common organic solvents, a member of a group consisting of ethylene glycols and alkyl ethers of the ethylene glycols and a common organic solvent as a dispersion medium.

11. A dye in organic dispersion as defined in claim 10, in which the dispersion medium is selected from a group consisting of alcohols and members of the benzene series of hydrocarbons.

12. A dye in organic dispersion as defined in claim 10, in which the dispersion medium is an alcohol. v

13. A dye in organic dispersion as defined in claim 10, in which the dispersion medium is benzene.

14. A dye in organic dispersion as defined in 16. A process 0! preparing a dye in organic dispersion which comprises mixing a dye material normally insoluble in the common organic solvents with a member of a group consisting oi the ethylene glycols and alkyl ethers of the ethylene glycols and diluting with a common organic solvent as-a dispersion medium.

17. A process of producing a dye in organic dispersion as defined in claim 16, in which the dispersion medium is selected from a group consisting oi. alcohols and members or the benzene series of hydrocarbons.

18. A process of producing dyes in organic dispersion as defined in claim 16. in which the dispersion medium is an alcohol.

19. A process of producing dyes in organic dispersion as defined in claim 16, in which the dispersion medium is benzene.

20. A process of producing dyes in organic dispersion as defined in claim 16. in which the dispersion medium is a lower alcohol.

21. A process of producing dyes in organic dis.- persion as defined in claim 16, in which the dispersion medium is a member of the benzene series oi hydrocarbons.

22. A composition adapted for the production or wood stains upon dispersion with a common organic solvent, said composition consisting of a dye material normally insoluble in the common organic solvents, and a member or a group consisting of ethylene glycols and alkyl ethers of the ethylene glycols.

23. A dye in organic dispersion comprising a water-soluble anilinedye, a volatile organic solvent thereior, a rapidly volatilizing organic nonsolvent component, the materials being present in proportions to yield a rapid drying and setting composition constituting a substantially light-fast, penetrating, non-bleeding, non-grain raising wood stain.

24. A combination wood stain and filler comprising a dye material normally insoluble in the common organic solvents, a member of a group consisting or ethylene glycols and alkyl ethers oi the ethylene glycols, a common organic solvent as a dispersion medium, and a wood filler.

25. A combination wood stain and filler com- 

